In fact, there are three other trophy penthouses at exactly $65 million currently on the market: 56 Leonard St.’s PH53/54 in Tribeca; 100 East 53rd St.’s #PH in Midtown East; and 995 Fifth Ave.’s #PH on the Upper East Side.

Trophy penthouses as part of collection

In addition to the same price tag, these penthouses have one more thing in common—collector quality, said Leonard Steinberg, president of Compass and listing agent of two of the penthouses, 56 Leonard St. and 100 East 53rd St. “They offer that Je Ne Sais Quoi that cannot be replicated, the essential hallmark of a masterpiece,” he said.

Masterpieces as they are, the four penthouses all benefit from prime locations, well-established developers, celebrity residents and above all, notable architects. Foster and Partners, Herzog & de Meuron and Robert A.M. Stern, architects for 100 East 53rd St., 56 Leonard St. and 70 Vestry, respectively, are currently behind many new major luxury residential towers around the world.

While 995 Fifth Ave. was originally designed by Rosario Candela who is credited with many of New York’s most prestigious Manhattan townhouses and penthouses built in 1920s, the building was converted by architect Madison Cox into a condop in 2005. It was originally the Stanhope Hotel.

Jonathan Miller, chief executive of real estate appraisal firm Miller Samuel, pinpoints at least one quality that these penthouses share that differentiates them from other apartments: “upper floor,” including private rooftops or wrap-around terraces.

Plus there are the unique layouts, high ceilings, fireplaces and other rare amenities that are not found in other apartments, all of which make them appealing to a very selective group of buyers.

The four $65 million penthouses do differ—namely on sub-location, size, price per square foot, as well as the amenities and lifestyles they offer.

“70 Vestry has spectacular, unobstructed views, high ceilings and the right market momentum, that explains why it has found a buyer first,” said Dolly Lenz, a broker and chief executive of Dolly Lenz Real Estate who isn’t involved in any of the sales of the four above-mentioned penthouses but is familiar with all of them.The other three either lack in “first-time excitement” or haven’t gotten off the ground, she said.

Out of the four penthouses, 70 Vestry, slated for completion next year, sold within five months after the listing. While 100 East 53rd St. is the only other brand new penthouse, it has been lingering on the market for 593 days, according to StreetEasy.

As a duplex combo, 56 Leonard penthouse has been on the market for 80 days, but the two apartments were resales and previously listed individually. 985 Fifth Ave. penthouse hit the market in May.

The most spacious and the least expensive penthouse by price per square foot is the combo duplex at 56 Leonard Street. The two units, previously listed for $30 million and $35 million, offer 11,892 square feet of living space together and command $5,465 for each square foot. Combined, the penthouse has eight bedrooms and nine bathrooms. The combo was listed in June.

“This duplex penthouse offers a quality of space only found in a mansion scaled townhouse but set over two floors, and 360-degree views that can never be replicated,” Mr. Steinberg said.

The smallest and most expensive penthouse in this exclusive group is at 100 East 53rd St. At 6,760 square feet, its average price per square foot equals $9,615. It has four bedrooms and four-and-a-half bathrooms.

The penthouse at 995 Fifth Ave. is ranked the second most expensive by price per square foot, asking $9,197 for each of its 7,067 square feet.

Penthouse South at 70 Vestry asked $8,384 per square foot before it went into contract at the end of July. The developer, Related Companies, declined to disclose the final sale prices.

Sizing up $65-Million Penthouses in Manhattan

Penthouse

Sq. Ft.

PPSF

DoM

Common Charge

Designer/Year/Developer

100E53rd #PH

6,760ft²

$9,615

593

$10,646

Foster and Partners/2017/RFR and Vanke

56 Leonard PH53/54

11,892ft²

$5,465

80

$12,623

Herzog & de Meuron/2015/Alexico Group and Hines

995 Fifth #PH

7,067ft²

$9,197

112

$38,430

Rosario Candela,1926/Madison Cox, 2005/Extell Development

70 vestry PHS

7,808ft²

$8,324

147

$14,717

Robert A.M. Stern/2018/Related Company

*Days on Market: Last listing as of September 11, 2017
Source: StreetEasy.com

High maintenance at 995 Fifth

Considering the cost of monthly maintenance, the penthouse at 995 Fifth Ave., the only condop out of the four that was converted from a historic building, is far more expensive, with a monthly maintenance of $38,430. The other three penthouses, all in new developments, range from $10,000 to $15,000 per month.

The high maintenance is partly due to the fact that the building is on leased land, according to Ms. Lenz. “It makes the property not an appreciating asset and deters buyers’ interest,” she said.

The penthouse is owned by Claude Wasserstein, whose late husband Bruce Wasserstein was the head of investment firm Lazard and owner of New York magazine. He purchased the penthouse for $34.8 million in 2008 and renovated the 11-room apartment.